


The Professional Cherry Popper

by Winchestersister1313



Category: Supernatural
Genre: AU, BDSM, Cuffs, Explicit Sexual Content, Light Bondage, M/M, Porn With Plot, Sex Work, Sex Worker Dean Winchester, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2021-03-17
Updated: 2021-03-17
Packaged: 2021-03-25 18:01:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,842
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30092967
Author URL: https://archiveofourown.org/users/Winchestersister1313/pseuds/Winchestersister1313
Summary: Dean loves his job helping people who are socially awkward with their first time. He gets more than he bargained for when he gets assigned to a man whose brother set up a "date".
Relationships: Castiel/Dean Winchester
Comments: 6
Kudos: 90





	The Professional Cherry Popper

**Author's Note:**

> This is a work of fiction some and all things mention may not be true to BDSM culture. please do your research before engaging in activities, kink responsibly.

** Chapter One **

Dean sighed with contentment as he left the apartment, another satisfied customer. He climbed into his car when his phone chimed a notification from the agency letting him know he had an appointment scheduled for the following day and an address and the client's profile. He headed home excited he had a new client also exhausted from the day's activities. Dean pulled into the driveway of his home, pressing the button to open the garage; pulling his beloved Impala inside, he turned the car off, closed the door. 

He kicked off his boots, lining them up by the door pulling off his black leather jacket. Everyone seemed to love hanging it up by the door; Dean wore it because it fit that whole bad boy image he had built for himself. He headed up the steps to the bedroom, stripping off his clothes and tossing them into the hamper before heading to the bathroom to take a shower. 

Dean Winchester was one of a kind in his profession. He was the one the agency called when they need to fulfill the bad boy fantasy. He exclusively saw virgins; he specialized in taking things slowly at their pace, teaching them different techniques with other partners. He loved his job, and the pay was amazing. The only problem it didn't leave much room for a social life. Dean had a few friends who knew what he did, but for the most part, he kept to himself. 

The following morning Dean checked the address to the new client again. Checking out the picture, the guy was cute, he thought to himself as he poured his morning coffee, heading back up to the bedroom, and opened the closet, pulling out a black t-shirt, black jeans with ripped knees. Getting dress, he headed back down to grab something to eat; the client had requested he come earlier than normal. He tossed a breakfast sandwich in the microwave, checking his watch. He was making a good time. Making sure the sandwich was hot before wrapping it in a paper towel. 

He grabbed his phone, wallet, and key, heading to the garage, slipping on his boots and lacing them up before pressing the button to open the garage. 

He got into the car, checking the address again; it wasn't too far from his house, about a thirty-minute drive depending on the traffic. Putting the key in the ignition, loving the sound of his baby roaring to life. 

Putting the car in reverse, he carefully pulled out of the garage, watching in case that kid from next door darted behind his car again. With the all-clear, he headed down the street, wondering what his new client was going to be like. He let his mind wander a bit; he prided himself on not getting attached. A few of his co-workers had found their person work. The once a month mandatory meeting that everyone had to attend to go over protocol, company policy, he had seen many people come and go. Dean always assumed he would forever be alone. Dean turned the corner. A large house sitting at the end of the block was his destination. As he pulled up to the curb, a man was standing on the porch. It wasn't the man in the picture; Dean turned the car off and looked at his phone, wondering if there was some two-for-one deal they forgot to tell him about. 

Dean looked up when there was a light knock on his window. It was the man from the porch, the man waved. Dean got out of the car, looking over the roof at the man. 

“My name is Gabriel; I hired you,” the man said, pointing to himself. 

“Ok, so I guess Castiel is your brother?” Dean asked, a bit confused about what was going on. 

“Yes, he is a bit shy. That's why I hired you,” Gabriel replied as he turned to head back up to the house. 

Dean furrowed his brow, pulling the keys out, locking the doors, and running after the man wondering what the hell was going on. Why did this guy call Dean for his brother? He took a deep breath. This wasn't new, but now he wanted to know if the brother even knew he was coming? If they agree to this or not?

“Ok, so Cas does know I was thinking about hiring you. He just doesn't know that i did it,” Gabriel said, opening the front door. 

“Woah, wait a sec, if he doesn't wanna do this, I'm not going to stay,” Dean said, stopping just inside of the door. 

“He does. It's just going to take some persuasion,” Gabriel smiled, wagging his eyebrows at Dean before turning heading down the hall. 

Dean took a second to think this over; he could find out what the guy wanted. Either way, he was still getting paid. He caught up to Gabriel after shutting the door. The house was hug on the inside; Gabriel turned and looked at Dean, “I'll go first,” he said with a nod like he was trying to convince himself this was a good idea. 

When the door opened, the man sitting at the table looked up; he had the bluest eyes Dean had ever seen; he was handsome, messy hair, and stern look on his face like he was disapproving of whatever his brother was about to say. 

“I..” Gabriel started to say when his brother held up his hand. 

“I don't care, I'm sorry for the inconvenience, but you can leave,” the messy-haired man said, glaring at his brother.

Dean didn't know what to say. The guy was beautiful. His voice, the cadence, the timber all off it sent shivers down his spine, “Um, ok,” he finally managed to say. Backing out of the room bumping into the wall, he didn't know why he was nervous; that man had something about him. He could hear Gabriel calling after him. Dean turned, looking at the shorter man. 

“He made it clear,” Dean said, throwing his arms up in the air. 

“Just let me talk to him first; like I said, this is going to take some convincing,” Gabriel said. 

“Fine,” Dean said, looking around. 

Gabriel led him to the living room tell him to wait there until he came back to let him know what his brother decides. He nodded, looking around the room. It was pristine. Everything had a place. The walls held random art that looked expensive. Family pictures lined the bookshelves and a few awards that Dean didn't take the time to read. Continued around the room, looking at the tiny beehives and bee knick-knacks that were on the shelves. He finally sat down on the couch. It was tan and looked like it had never been used spotting the DVD collection. Dean got back up, heading over to see what movies this guy had. 

“Gabriel tells me your name is Dean,” the rough voice said, scaring the shit out of Dean. 

Dean grabbed his chest, turning to look at the man; he was a work of art in Dean's eyes. Perfect jawline, plush pillow lips, those fucking eyes that Dean knew would stick with him for the of his life, “Yeah, that's my name,” he mumbled; his throat was dry. How was this man a virgin? There was no way. The way the man looked at him like he was prey turned Dean on, a kink he didn't know he had. 

“Come back tomorrow. We can talk about your services,” Castiel said before turning and leaving the room. 

Dean stood there for a moment before heading to the front door, his phone vibrating in his pocket, letting him know the “date” was set up for tomorrow. This was a first he could wait to come back; he wanted to be near the man again. 

*************

Dean looked up at the house. There was something different about it today, not scary, maybe scar, intimidating he was all Dean could think about. It was strange the feeling he got seeing the man. It was like he was supposed to be where they were supposed to be together. He made his way out of the car and up the steps knocking on the door. He waited, expecting to see Gabriel again. He was greeted by Castiel, who was wearing a t-shirt and grey sweats, “Hello, Dean,” he greeted in his raspy timbre. 

“Hey, Cas,” Dean replied with a smile. 

The man tilted his head to the side and gave a soft smile, “Follow me; I think we should talk before we get started,” Cas said, turning on his heel and heading in the direction Dean knew was the kitchen. 

Cas pointed to the chair at the table, indicating for Dean to sit before asking if he would like a drink or something to eat; Dean shook his head, saying no, he was good. The other man grabbed a cup, pouring himself some coffee before joining Dean at the table. 

“So my brother tells me you are the guy they call in for virgins,” Cas stated, taking a sip of his drink. 

“Yup, I'm a bit gentler than the others,” Dean replied; he was not ashamed to admit he had a soft side. 

“I'm not a virgin; my brother thinks I am because he has never met any of my partners,” Cas said, setting his cup down on the table.

Dean didn't know what to say, but relief rushed through him at the thought of possibly having sex with someone experienced; it had been a while for him it would be a nice change. “If you don't mind me asking, why hasn't your brother met anyone?” he asked, not sure if he was crossing a line, but he needed to know why. 

Cas sighed, taking another sip of hot liquid, “I'm a Dom, and not a lot of people are open about their lifestyle; I respect it,” he replied after swallowing. 

If the thought of this man using Dean as he pleased didn't turn him on, he would be lying; he had always been curious about BDSM but never explored it; with work, he never found the time. When he didn't reply, Cas cleared his throat. Dean looked up at the man across from him, hoping he would ask him to stay and they could have a good time. 

“Are you ok?” Cas asked, watching the different emotions play out over Dean's face. 

Dean cleared his throat, rubbing the back of his neck, not looking up at Cas. He nodded; it was strange. All they were doing was talking, but the simple sound of the man's voice was making Dean chub up. 

“You don't seem ok,” Cas said, watching the man's reaction. 

“Um, well... I uh-” Dean cleared his throat, “You aren't what I expected; I mean, it's a nice change but not my normal gig,” he finished looking up from his hands. 

Cas nodded slowly, “If you want to leave, I will still pay you, but if you want to stay, we can start light,” he said, getting up from his chair taking his cup to the sink. 

“What did you have in mind?” Dean asked, curiosity burning in him to know what was going to happen next. 

Cas smiled and rubbed a finger across his bottom lip, “Follow me,” he said, turning and heading back down the hall; Dean scrambled out of the chair to follow the man. 

He took a steadying breath as the excitement of something new and unexpected started to settle in. Dean followed close as Cas made his way up the stairs turning and heading to a door with three small steps in front of it. “If there is anything I should know, tell me now, medical conditions anything?” Cas questioned. 

“Nah, I'm good, I'm curious,” Dean replied with a flirty smile. 

“I bet you are,” Cas said, opening the door. 

Dean was taken back at the room's vastness; he was shocked that a huge bed was in the middle. There was still room to walk around; he looked at everything; Cas told him it was fine to touch things get familiar with everything. Any questions he was free to ask, Dean smiled, saying that was usually his line. The walls were organized better than Dean's whole house, ropes of varying lengths and colors grouped together. There were varying cuffs for the wrist and ankles. Dean ran his fingers over the fur lines ones wondering what it would feel like on his skin. 

“Those are my favorite,” Cas said from behind Dean. He was so close he could feel the heat of his breath on his neck. 

Dean licked his lips, moving along the wall, floggers, and paddles; he loved a good slap on the ass. He wondered if Cas could do it better. Canes and horse crops were next hanging ominously. He was too sure about those, but the others were definitely on his try list. There was a bench with cuffs a cage under the bed. He looked at Cas and pointed. 

“I have had a few partners into pet play; it was relaxing to let themselves go for a bit,” Cas replied. 

“I could see that,” Dean replied, “What's in here?” he opened the top drawer of the dresser. He was greeted by anal beads and a few plugs; the next drawer was dildos of different girths. Dean was more than willing to try those; he had one at home for the times he leaves less than satisfied, but in truth, it was all about getting the client off. That was what he was getting paid for. 

“So, wanna stay?” Cas asked. 

“I got questions,” Dean replied. 

“I would be worried if you didn't,” Cas smiled, heading over to the bed, patting the spot next to him for Dean to sit down. 

Dean sat down, playing with the zipper on his jacket, unsure what to ask. Now that he had the chance, he figured asking if Cas wanted this to be a one-time thing or what he wanted out of it. Cas smiled, saying that was up to Dean as well. He was more than happy to find out if they were compatible in the bedroom before committing to a full-time thing. Still, he informed Dean that he didn't share well, so he would have to find a different job if he wanted to his Sub. It was just how Cas was. Dean nodded to say he understood that would make sense seeing as how his profession could interfere. They talked a bit more Cas said there was no need to commit today, but he was curious if Dean was a good fit. 

“What do you want me to call you?” Dean asked. 

“Cas is fine for now; we can talk honorifics when we get there,” Cas replied with a smile, “if you want, we can start.”

Dean nodded, “I would like that.”

Cas instructed Dean to get undressed, fold his clothes and place them on the dresser, his boots on the floor next to the dresser. He was sure Dean showered before showing up but then told him to make sure there was a bathroom where he could freshen up. Dean did as he was told, looking at himself in the mirror, his face flushed with the excitement of what was to come. Making sure he was clean and ready for Cas, he headed back out to the room. 

“Such a good boy,” Cas purred, making his way over to Dean. Circling him like a vulture that found food, Dean felt exposed, and he loved it. “Look at you, I haven't even touched you, and you are hard.,” the Dom said, running a fingertip down Dean's length making the man whimper.

Dean didn't even know he could make that noise, but between the excitement of a new adventure and the man's voice, he was surprised that he hadn't cum already. Dean couldn't remember the last time he was this turned on. Cas finally stopped circling him; standing behind Dean, he could feel the man ghosting his fingertips along the lines of his shoulder and down his sides. Dean closed his eyes, letting the feeling wash over him. Cas wrapped his arms around his middle, running his hands up and down his chest, pinching his nipple. Dean hissed at the pain but was also turned on a bit. 

Cas chuckled, “That's what I thought; I'm good at reading people,” he said in Dean's ear, his lips brushing against the shell of his ear, “Did you like that?”

Dean nodded; hell ya, he wanted Cas to do it again. He wanted this man's hands all over his body, never-ending feeling whatever this was; he wanted it all the time. He sighed as Cas slid his hand down his stomach, kissing the side of his neck, enjoying the feeling of stubble scraping. The sensation was out of this world. If someone asked, Dean wouldn't know what to say. His senses were in overload. The hushed tones Cas was speaking in when asking questions made Dean feel at ease; the rough callouses on his hands were a nice contrast from the past few weeks of woman he had been with. 

“So beautiful, Dean, such a good boy,” Cas praised smack Dean on the ass. 

“Ah,” Dean cried out, loving the way his skin heated up. 

“Mmm, you like that,” Cas asked, repeating the assault again. 

Dean moaned, reaching down and gripping his erection to stop himself from cumming; Cas grabbed his wrist, holding on until he was ready for them to continue. “I think a cock ring is needed. What do you think?” Cas asked, stepping to the side. 

“I agree,” Dean replied, breathing deeply calming himself. This was not what he was expecting, but damn, if he wasn't happy, Cas’s brother thought he was a virgin. 

Dean sighed as Cas place a kiss on his shoulder before moving away to the dresser. Opening the top drawer pulling out a ring before making his way back over to where Dean was waiting. 

“Are you ok? Would you like to continue?” Cas asked before slipping the ring on Dean. 

“Please,” Dean replied, “I'm good.”

Cas hummed with approval, moving back around Dean., “You'll look so pretty tied up,” he commented in an amused tone. 

The air was trapped in Dean's chest. He had never in a million years thought the words coming out of Cas’s mouth would turn him on so much. He moaned as Cas resummed his assault on Dean's body, rubbing, pinching, whispering sweet words of praise that Dean had never heard in his life. 

“Get on the bed,” Cas said, giving Dean a slight push in the shoulder. 

Dean felt like he was floating the feeling was surreal; he loved it. He also wondered if this is what his clients felt when he was with them; he climbed up on the bed waiting for Cas to tell him where he wanted him, “Good boy, waiting for me. On your back,” Cas said, removing his shirt. 

Dean laid down, looking up at the ceiling. He didn't notice the mirror until now, looking away when he felt a dip in the mattress. Cas climbing towards him with the cuffs he was admiring in his hand. Without hesitation, Dean raised his arms above his head, earning him a smile from Cas. 

“Dean, you are by far the best partner I have had,” Cas said, bucking one of the man's wrists. 

“Thank you,” Dean smiled, feeling his flesh heat up from the compliment. 

Once he was done fastening the cuffs, Dean watched as Cas moved back down, moving Dean's legs, so they were draped over his shoulders, running his hand up and down Dean's legs admiring the man below him, squirmed a bit under the man's gaze. Dean was unsure what he was supposed to be doing. This was new for him. 

“Are you ok?” Cas asked, kissing Dean's calf. 

“Yes, I'm ok,” Dean replied. 

“Good,” Cas replied, leaning down. 

Dean moaned in surprise as the man's mouth engulfed his length; this was not what Dean was expecting; he was usually the one performing the services, “Oh fuck,” he cried out as Cas licked him from balls to tip. Dean knew he was ruined, at least for blow jobs by this guy fuck. If he wasn't wearing the cock ring, he would have cum several times by now. Dean whimpered when he felt Cas make his way to his ass, pulling the plump globes apart before giving it a lick. 

Yeah, Dean was ruined by this man; he did things that Dean had never thought of. The floaty feeling was amazing. He wanted to feel like that all the time, closing his eyes, enjoying the way Cas teased his hole, pressing the pad of his finger against him before pulling away. It was frustrating and titillating all the same; he wanted more he wanted to feel the man buried deep inside of him, stretching him, making him beg to cum. He jumped when the feeling of cold lube touched his hole. It was unexpected and welcoming, meaning that they were about to get to the good part. 

“Good boy, relax,” Cas said, running his hand up and down Dean's stomach while his other hand working Dean open. 

“Oh,” was all Dean could manage when Cas twisted his finger, finding his sweet spot. 

He could feel Cas smile against his skin as he gave Dean's cock one last lick. Dean opened his eyes, watching as Cas moved to his knees. He held his breath as the man lined himself up, pushing in slightly and pulling back out. 

“Please,” Dean begged. He wasn't normally so needed, but fuck, he needed to cum. 

“Please what?” Cas asked, biting his bottom lip with a small smirk playing on his lips. 

“Please, fuck me,” Dean panted out. The anticipation was killing him. 

Cas smiled and pushed in, making Dean groan with pleasure. The man wasn't small. No wonder he spent so much time prepping Dean. The pace was amazing slow but building as he pulled against the restraints wanting to feel Cas’s skin behind his hands. He needed the contact o know this was really happening that the pleasure was, in fact, real; he sighed, feeling Cas press his lips to his in a soft kiss; it was like he could read Dean's mind. He knew what he needed. 

“You can cum when you want,” Cas grunted, kneeling as he adjusted the angle, pulling the cock ring off before holding up Dean's hips to get in deeper. 

It didn't take too long for Dean to cum, seeing stars as the pleasure erupted from him. Cas lasted a bit longer from what Dean could tell. He barely heard the praise as Cas unbuckled his wrists, rubbing them, making sure he was ok. 

“Sleepy?” Cas asked, wrapping Dean in a blanket. 

“Mmm, yes,” Dean mumbled. 

“We will talk when you waked up.”

**Author's Note:**

> Thanks for reading. 
> 
> Comments, Kudos, and questions are always welcome. 
> 
> I have Grammarly set to "Informal" to allow bends in the rules.


End file.
